phenylsulfonylacetyl chloride | 72263-17-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenylsulfonylacetyl chloride
• 英文别名: 2-(Benzenesulfonyl)acetyl chloride
• CAS: 72263-17-3
• 化学式: C₈H₇ClO₃S
• 分子量: 218.661
• InChiKey: MUAMDZUOJVJJGI-UHFFFAOYSA-N

物化性质

• 沸点：
  374.5±34.0 °C(Predicted)
• 密度：
  1.399±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  phenylsulfonylacetyl chloride 在 4-乙酰氨基苯磺酰叠氮 、 三乙胺 作用下， 以 乙腈 、 苯 为溶剂， 反应 8.0h， 生成 1-(2-benzenesulfonyl-2-diazoacetyl)pyrrolidin-2-one
  参考文献：
  名称：

  An Isomünchnone-Based Method for the Synthesis of Highly Substituted 2(1H)-Pyridones

  摘要：

  1-(Benzenesulfonyl-diazoacetyl)-pyrrolidin-2-one was prepared by a diazo transfer of 1-(benzenesulfonylacetyl)-pyrrolidin-2-one with p-acetamidobenzenesulfonyl azide and triethylamine. Treatment; of the diazoimide with a catalytic quantity of rhodium(II) acetate resulted in the formation of an isomunchnone dipole, which underwent bimolecular trapping with various dipolarophiles in high yield. The initially formed cycloadducts were not isolable or observed, as they all readily underwent ring opening to give the 3-hydroxy-2(1H)-pyridone ring system. The 3-hydroxy-2(1H)-pyridones were readily converted to the corresponding triflates, which function as suitable substrates in various types of palladium-catalyzed cross-coupling reactions. Commercial tetrakis(triphenylphoshine)palladium was found to be a particularly effective catalyst for the cross-coupling with aryl, vinyl, and acetylenic partners. An application of the method to the synthesis of the indolizidine alkaloid (+/-)-ipalbidine was carried out in eight steps in 17% overall yield. The angiotensin-converting enzyme inhibitor (-)-A58365A was also synthesized by a process based on the [3 + 2]-cycloaddition reaction of a phenylsulfonyl substituted isomunchnone intermediate. The starting material for this process was prepared from L-pyroglutamic acid and involved using a diazo phenylsulfonyl substituted pyrrolidine imide. Treatment of the diazoimide with Rh-2(OAc)(4) in the presence of methyl vinyl ketone afforded a 3-hydroxy-2-pyridone derivative, which was subsequently converted to the ACE inhibitor in six additional steps.

  DOI：

  10.1021/jo9911600
• 作为产物：
  描述：

  (苯磺酰)乙酸 在 草酰氯 作用下， 反应 1.0h， 生成 phenylsulfonylacetyl chloride
  参考文献：
  名称：

  从无环（戊二烯基）铁（1+）阳离子制备环己酮：针对二氢速甾醇 A 环的合成研究

  摘要：

  三羰基（3-甲基戊二烯基）铁（1+）阳离子 (7) 与稳定的碳亲核试剂反应得到 4-甲基-5-取代的环己烯酮。7与双[(+)-2-苯基环己基]丙二酸钠反应得到非对映体混合物(de = 60%)；由该混合物的 Luche 还原产生的非对映烯丙醇可通过柱色谱分离。报道了来自这些环己烯酮的速甾醇 A 环合成子的非对映选择性问题。

  DOI：

  10.1002/ejoc.201402615

文献信息

• Stereoselective synthesis of 2,4-disubstituted butanolides
  作者：A. V. Lozanova、T. M. Ugurchieva、V. V. Veselovsky

  DOI：10.1007/s11172-007-0021-4

  日期：2007.1

  A series of 2,4-disubstituted butanolides was prepared based on the trans-stereoselective electrophilic cyclization of substituted N-(pent-4-enoyl)pyrrolidines. The butanolides may be considered as synthons for this type of natural products.

  基于取代的 N-(pent-4-enoyl) 吡咯烷的反式立体选择性亲电环化制备了一系列 2,4-二取代丁醇内酯。丁醇内酯可被视为此类天然产物的合成子。
• Palladium-Catalyzed [3 + 2]-C–C/N–C Bond-Forming Annulation
  作者：Yang Liu、Zhongyi Mao、Alexandre Pradal、Pei-Qiang Huang、Julie Oble、Giovanni Poli

  DOI：10.1021/acs.orglett.8b01616

  日期：2018.7.6

  The synthesis of bi- and tricyclic structures incorporating pyrrolidone rings is disclosed, starting from resonance-stabilized acetamides and cyclic α,β-unsaturated-γ-oxycarbonyl derivatives. This process involves an intermolecular Tsuji–Trost allylation/intramolecular nitrogen 1,4-addition sequence. Crucial for the success of this bis-nucleophile/bis-electrophile [3 + 2] annulation is its well-defined

  从共振稳定的乙酰胺和环状α，β-不饱和-γ-氧羰基衍生物开始，公开了掺入吡咯烷酮环的双环和三环结构的合成。该过程涉及分子间的Tsuji-Trost烯丙基化/分子内的氮1,4-加成序列。这种双亲核试剂/双亲电子试剂[3 + 2]的成功成功的关键是其明确定义的步骤时间顺序以及前一步的总化学选择性。当新形成的环状产物在氮取代基上带有适当定位的邻卤代芳基部分时，另一分子内的酮基α-芳基化反应可加入级联反应，从而在同一合成操作中形成两个新的环和三个新的键。
• Ligand effects in the rhodium(II) catalysed reactions of diazoamides and diazoimides
  作者：Soyfur Miah、Alexandra M.Z. Slawin、Christopher J. Moody、Scott M. Sheehan、Joseph P. Marino、Mark A. Semones、Albert Padwa、Ian C. Richards

  DOI：10.1016/0040-4020(95)01070-x

  日期：1996.2

  ligands, fluorinated carboxamides strongly promoting attack on aromatic rings in preference to other processes. Decomposition of the diazoimides resulted in intramolecular attack on the carbonyl group to give an ylide which could be trapped inter- or intramolecularly. X-Ray crystal structures are reported for the diazo compounds 2 and 4, the indoles 17 and 25, the β-lactam 20, the cycloheptapyrrolones 24

  由相应的胺或酰胺制备了一系列取代的α-重氮酰胺1-8和重氮酰亚胺9-12。铑（II）催化的重氮酰胺分解导致对芳环的进攻，从而产生羟吲哚或对烷基的进攻，从而产生β-内酰胺或环庚吡咯烷酮。铑类胡萝卜素中间体的化学选择性取决于金属配体，氟化羧酰胺优先于其他过程而强烈促进对芳环的攻击。重氮酰亚胺的分解导致分子内对羰基的攻击，从而产生可被分子间或分子内捕获的叶立德。据报道重氮化合物2和X的X射线晶体结构如图4所示，吲哚17和25，β-内酰胺20，环庚基吡咯烷酮24和28，二聚体29和Pictet Spengler产物39。
• A Base-induced Elimination Reaction of Phenylsulfonylacetates. I. General Aspect and Stereochemistry
  作者：Akira Sera、Hiroshi Mano、Kazuhiro Maruyama

  DOI：10.1246/bcsj.47.1754

  日期：1974.7

  t-butoxide in t-butyl alcohol. The intervention of a carbanion as an intermediate of the elimination was proposed. The stereochemistry of the elimination was examined by the use of erythro and threo-2-deuterio-1,2-diphenylethyl phenylsulfonylacetates. From the deuterium content in a product, i.e., trans-stilhene, the elimination was found to occur predominantly in a syn fashion.

  发现苯磺酰乙酸酯与叔丁醇中的叔丁醇发生碱诱导的 β-消除反应。建议将碳负离子作为消除的中间体进行干预。通过使用 erythro 和 threo-2-deuterio-1,2-diphenylethyl phenylsulfonylacetates 检查消除的立体化学。从产品，即反式二苯乙烯中的氘含量，发现主要以顺式方式消除。
• Amine Derivatives as Potassium Channel Blockers
  申请人：Harvey Andrew

  公开号：US20140336198A1

  公开（公告）日：2014-11-13

  The present invention relates to compounds useful in the modulation of potassium channel activity in cells, in particular the activity of Kv1.3 channels found in T cells. The invention also relates to the use of these compounds in the treatment or prevention of autoimmune and inflammatory diseases, including multiple sclerosis, pharmaceutical compositions containing these compounds and methods for their preparation.

  本发明涉及用于调节细胞中钾通道活性的化合物，特别是用于调节T细胞中发现的Kv1.3通道活性的化合物。本发明还涉及使用这些化合物治疗或预防自身免疫和炎症性疾病，包括多发性硬化症，含有这些化合物的制药组合物以及它们的制备方法。